Flotation of barite



United States Patent 0 3,1225% FLGTATHGN @F BAEQETE n ames T. Guilett,lvialvern, Arie, and William A. Reduie,

Houston, Tex, assignors to Magnet Cove Barium Qorporation, Houston, Tex.No Drawing. Filed Jan. 24, 1962, Ser. No. 168,531

3 Claims. (Cl. 2il9-166) This invention relates to the flotation ofbarite from gangue contained in its ores and is particularly directed toa novel combination of collection agents which is highly emcient incarrying out this process.

The process of beneficiating ores by means of froth flotation is old andwell known and has been applied to the beneficiation of a great manyores. Briefly, it may be considered a process wherein an ore is finelyground and the resulting fine material is suspended in water to form afluid pulp, and the entire mass is agitated and aerated in the presenceof a collector and a frothing agent to form a froth floating on thesurface of the liquid. In a process of this type, the collector must besuch that it attaches itself to the surface of the heavy mineralparticles, thus giving the mineral particles a hydrocarbon-like surfacelayer, usually of monomolecular thickness, which is capable of adheringto air bubbles and carrying the heavy mineral upward into the frothwhere it may be skimmed off by any suitable skimming device. It isobvious that the collector used for the beneficiation of any particularore must be highly selective, so as to form films upon the surface ofthe desired mineral only and not upon the gangue, thus floating only themineral particles allowing the gangue to remain at the bottom of theliquid.

Barite, or native barium sulfate, is an important mineral with wideindustrial applications. Many of the higher grade deposits of barite inthe United States have been worked out and miners of this material havebeen forced to obtain more and more barite from increasingly poorer orebodies with the result that froth flotation for the beneficiation ofbarite is becoming increasingly more necessary.

in one of the principal processes for benefication of barite ores, thatis, the preparation of barite for use as a weighting material in thedrilling of oil and gas wells, the barite product must have a very highspecific gravity; and since the gangue is usually of much lower gravitythan the barite, it must be well separated from the barite ore so thatthe barite sold for this purpose should have a specific gravity of 4.25or more.

Collectors for use in the barite flotation process should not only beefficient and highly selective, but also should be easily removable fromthe barite. Fatty acid soaps and certain combinations of fatty acidshave been used and have been found to be excellent collectors for use inthis process. The fatty acids, however, are hard to remove after theflotation process has been completed; and removal must be substantiallycomplete, otherwise the purified barite is not Wettable by water and isunfit for drilling mud use. Both chemical and mechanical methods ofremoving fatty acid residues have been tried. Among these methods,drying at high temperature has proved to be most economical, but attemperatures in excess of 600 F. some reaction occurs with increase inproportion of soluble salts in the product. The presence of solublesalts in barite is highly objectionable in the drilling mud field.

3,3225% Fatented Feb. 25, 1964 Certain mixtures of fatty acids and longchain organic sulfates, such as cetyl sulfate and stearyl half sulfate,have been used and found to be excellent collecting materials, specificin their collecting action for barium sulfate and easily removable fromthe beneficiated mineral at temperatures sufficiently low to preventexcessive formation of soluble barium salts. These sulfates, however,are quite expensive in the quantities used; and it is always desirableto lower the cost of beneficiating any mineral. Also, these sulfates arepastes at ordinary temperatures and are diflicult to dissolve in water,especially under winter conditions when the water is cold.

It is therefore one object of this invention to provide a novel mixtureof collecting materials for use in a bar-ite flotation process in whichthe materials used are readily available and cheap, and which are highlyeflicient when used together.

Another object is to provide a novel combination of materials for use asa collector in the barite flotation process which are highly selectivefor barite and are easily removable from the barite after separationfrom gangue.

Another object is to provide a novel combination of collector materialsfor use in the flotation of barite which eliminates or greatly reducesthe quantity of frothing agent required.

Another object is to provide such novel mixture of materials which giveexceptionally high yield of barite and are cheap enough to eliminate thedesirability of heating process water during winter operations in orderto reduce the quantity of reagents required.

Another object is to provide such mixture of materials in which thematerials are liquid at ordinary room temperatures and are easilysoluble in the coldest water.

Other objects, advantages and features will be apparent to one skilledin the art upon studying this specification and the appended claims.

In the process of the present invention, barite is separated from ganguein a finely divided ore by frothfiotation in the presence of a mixtureof a sodium salt of sulfated dinonylphenol still bottoms adducted withethylene oxide and a fatty acid having from 8 to 20 carbon atoms permolecule. The mixture of sulfated dinonylphenol still bottoms adduct andfatty acid serves as a highly efficient collector. This mixture not onlyis highly specific for barium sulfate to give a high purity product butis very easy to remove from the barite after separation in froth. Bothmaterials are liquids and the mixture is easily soluble in Water at alltemperatures above the freezing point.

A mixture of the sulfated still bottoms adduct and fatty acid is fullyequivalent in efiiciency to the best collecting agents for bariumsulfate known at present and is extremely easy to remove from thepurified barite. The froth has excellent mechanical properties and verysmall quantities of the mixture of collecting agents are required. Inaddition, these materials are so cheap that the over-all cost ofconducting the process is noticeably lowered and heating process waterduring winter operations to reduce consumption of reagents or todissolve the required amounts of reagent in water is eliminated aseconomically undesirable, since the additional quantities required forwinter operation are so small that their cost is less than that ofheating the water.

The ratio of sulfated still bottoms adduct to fatty acids areaeoo may beanywhere in the range from 10:1 to 1:2, but is preferably in the rangefrom about 2:1 to 1:2. The fatty acids are even cheaper than thesulfated still hottoms adduct and for economic reasons, it is preferredto use as large a proportion of the fatty acids to still bottoms adductas can be utilized with good results.

The fatty acid portion or" the collector may be any readily availablefatty acid having from 3 to 20 carbon atoms per molecule and may besaturated or unsaturated. Preferably, the fatty acid component is amixture of fatty acids such as are available on the market as fattyacids from coconut oil, fatty acids from cottonseed oil, crude oleicacid, fatty acids from corn oi. or any or" the other available mixturesof fatty acids in this carbon atom range. The preferred fatty acidproduct is a mixture of fatty acids distilled from tall il. Thecommercial products containing these acids from tall oil ordinarilycontain about 50 percent oleic acid, 40 percent linoleic acid, about 4percent linolenic acid and have a residual rosin acid content of about 6percent. In this mixture, the rosin acids do not interfere, and we havefound that it not only is a highly eilicient collector when used inconjunction with the sulfated still bottoms adduct but is very easilyremovable from the concentrated barite.

Preferably, the fatty acids may be added to the pulp as such rather thanin form of fatty acid soaps, but there will be at least some conversionof the acids to soaps in the pulp since the flotation of barite isusually conducted in the pH range from 8.0 to 12.0 or preferably in thepll range from about 9.5 to 11.0. An alkaline mateial, preferably sodiumhydro 'de, is used in quantity reuired to give a selected pH in therange described above. The quantity of such alkaline material used willvary somewhat depending upon the particular ore being beneiiclated andtheweather conditions. A slime dispersant, such as sodium silicate, alsois used in conventional manner. Preferably, the sodium hydroxide andsodium silicate are added in a first conditioner in the flotationcircuit, and the materials used as collecting agents are added in asecond conditioner.

A suspension of the finely ground ore is introduced into a thicker and aconventional flocculant, as, for example, a mixture of high In lecularweight polyacrylarnides, is added in quantity sufficient to fiocculateand thicken the pulp to a desired degree. The resulting thickened pulpis then passed to a first conditioner where an alkali hydroxide and theslime dispers at are added. The alkaline pulp then is passed to a secondconditioning tank Where the collecting agents of the present inventionare added. The fatty acid material and the alkali salt of sulfatednonylphenol still bottoms adduct preferably are added separately to savea mixing step and for convenience in control, but they may be pre-mixedand added together if desired. The resulting suspension then is passedthrough a series of flotation cells Where it is agitated and blown witha gas such as compressed air and barite is separated from gangue and isfloated in resulting froth.

Normally, a frothing agent will be f und unnecessary when the mixture ofcollecting agents of this invention is used, but occasionally underparticularly adverse conditions a small amount of nothing agent may benecessary. When required, the trother may be a low molecular Weightalcohol, as, for example, isopropyl alcohol, am '1 alcohol, or apolypropylene glycol methyl ester marketed under the trade nameDow-broth. In actual plant operation, it has been found that it isusually unnecessary to use a frothing agent, but in about 5 percent ofactual operating time when conditions were particularly adverse, a smallamount or" conventional frothing agent was necessary for best results.

It will be seen that the steps of the process just described areconventional except for the use of t. e particular collecting agents ofthe present invention which decrease the cost, eliminate the necessityfor Warming the Water use under w nter conditions, eliminate or decreasethe quan- .1 tity of frother normally required by performing thefunctions of both collector and frother, and decrease the difficulty ofdissolving the collector agent in Water.

The still bottoms adduct used in preparing the sodium salt of thesuliated still bottoms adduct component of the mixture of flotationagents is prepared from a still bottoms derived from a phenol alkylationprocess. In a process of this type, phenol is alltylated with an alk-eneof desired length and configuration to yield predominantly thecorresponding alkylphenol and dialkylphenol. In this reaction, productshaving higher boiling points than that of the dialkylphenol are formedalso, and v ill be present in the still bottoms residue. The exactcomposition of these high boiling products is not known, but it is knownthat they are produced in the above-described phenol alkylation process.

it is customary to distill the reaction mixture resulting from thephenol alkylation reaction to recover an overhead product. The principalmaterial recovered in the first part of the distilla ion will bemonoalkylphenol although this may be preceded by small amounts of unreacted alkene or phenol or both. stopped at this point, as it frequentlyis in commercial practice, the remaining still bottoms product willcontain dialkylphenol, any monoalkylphenol which did not pass offoverhead during the first part of the distillation and a residue ofproducts having higher boiling points than that of the dialltylphcno-l.The relative proportions or" these three components Will vary with theefficiency of the a kylation process and of the fractional distillation.

Generally, these still bottoms are derived from proc esses foralkylating phenol with a polymerized alkene wherein the alkenepolymerized contains a number or" carbon atoms in the range from 2 to 4.The alkene reactant can be either a branched or straight chainhydrocarbon. derived from alkylation of phenol with butene, pentene,hexene, octene, nonene, dodecene, pentadecene, hexadeccne, octadecene,etc. The preferred material, however, is still bottoms derived from afractionation of nonylphenol described below.

In View of the foregoing, the term al iylphenol still bottoms will beused in th s specification and claims to embrace all still bottoms fromdistillation processes for separating products resulting from alkylationof phenol With C to C alkenes to produce one or boththe correspondingmonoalkylphenols or dialkylphenols as above disclosed where such-stillbottoms comprises a hi h boiling residue, either in a substantially pureform'or mixed with from O to 5 parts of the corresponding dialkylpbenoland/or with O to -10 parts'or" the corresponding monoalkylphenol, theresidue in-any case being'present in the still bottoms in an amount ofat least 5 percent of the total still bottoms, said residue having aboiling point or range higher than that of the correspondingdialkylphenol.

The still bottoms oxyethylene adduct is more eihecient as a component ofthe barium sulfate collector than a similar adduct of eithermonoalkylphenol or dialkylphenol. Apparently, the high efliciency comesfrom the presence of high molecular weight materials inthe still bottomsresidue although these are of unknown composiion.

A preferred method for the preparation of the alkyl phenol still bottomsadduct is to adduct the still bottoms from a process for producingnonylphenol with from 1.5. to 3.0, preferably about 2, parts ofoxyethylene per part;

i still'bottoms. A preferred still bottoms residue, which iscommercially available at present, is derived as a byproduct in thepreparation of nonylphenol by the following process.

In this preparation, one common practice is to polymerize propylene toprovide a nonene comprising a very high percentage of 9-carbon chaintn'mer of propylene. Other nonenes can be used if desired. The nonene isIf the fractionation is t Examples of this class are stillbottomsreacted with phenol in the prescence of a catalyst, such assulfuric acid or boron trilluoride. A mixture of alkylated phenolsresults which is then distilled to produce an overhead productcomprising relatively pure nonylphenol. The still bottoms from thisfractionation comprises any portion of the nonylphenol not distilledover, dinonylphenol and a residue of higher boiling materials which maycontain pol merized phenols, alkylates of phenols which are higherboiling than dinonylphenol, complex benzene compounds and the like.

It will be apparent that the amount of nonylphenol in the still bottomswill vary with the efficiency of the alkylation process and of thesubsequent fractionation step. By suitable fractionation procedure, thenonylphenol can be completely removed, leaving the still bottomscomprising dinonylphenol and residue. With still further distillation, apart or all the dinonylphenol can be removed, leaving a still bottomscomprising a substantially pure residue. Such fractionation usually isconducted under a vacuum of about to 20 mm. of mercury and at afractionator head temperature of not less than 200 C., such temperaturebeing determined by the boiling point of the fraction removed overhead.

The alkylate from the nonylphenol process should be fractionated untilat least 50 percent of the nonylphenol produced is removed as anoverhead, leaving the remainder as still bottoms. utated numerically,the nonylphenol still bottoms can comprise the high boiling residue,either pure or mixed, for each part of residue with from 0 to 10 partsof dinonylphenl and/or with O to 5 parts of nonylphenol, the residue inany case being present in an amount of at least 5 weight percent of thetotal still bottoms. Either or both dinonylphenol or nonylphenol can bepresent with the residue.

One specific still bottoms found useful contained 30 percentnonylphenol, 50 percent dinonylpheuol and 20 percent high boilingresidue, and nonylphenol still bottoms commercially available ordinarilywill contain from about percent to about 30 percent of nonylphenol withthe balance being made up of dinonylphenol and high boiling residue, thedinonylphenol comprising the major portion of the balance, with theresidue varying from at least 5 up to percent or more.

The reaction between the alkyl still bottoms and the ethylene oxide iswell known to those slc'lled in the art, and commercial products of thisreaction are readily available on the market. One product of this typeis sold commercially under the designation OX153 l2. It is a stillbottoms from the above-described nonylphenol process and is adductedwith 2 parts by weight of ethylene oxide per weight of still bottoms.

The still bottoms comprising the residue and the dinonylphenol, if any,and the diluent nonylphenol, if any, is then reacted with oxyethylene.The amount of oxyethylene so reacted should be in the range from about1.5 to 3.0, preferably about 2, parts per weight of the still bottomsbeing adducted. Where the still bottoms is rich in residue, the amountof oxyethylene should be chosen from the higher portion of this range.Where it becomes richer in dinonylphenol or in nouylphenol, the amountmay be chosen from a lower portion of the range.

The nonylphenol still bottoms is reacted with ethylene oxide in thefollowing manner: The nonylphenol still bottoms is charged into asuitable reaction vessel and about 2 percent or a little less of analkaline hydroxide is added. The reaction vessel is then thoroughlypurged with natural gas or other inert gas suitable for removing airwhile the temperature is elevated to about 156 C. The addition ofethylene oxide to the reactor vessel is commenced at this temperature,and the reaction mixture is maintained in the temperature range from 150to 160 C. until the entire quantity of ethylene oxide desired has beenadded. The reactor contents are then recycled for about two hours inthis temperature range. At the end of the reaction period, glacialacetic acid is added in quantity to neutralize the adduct.

In converting the intermediate product from the reaction described aboveto the sulfated material of the present invention, the ethoxylatednonylphenol still bottoms residue is charged into a suitable reactionvessel and the temperature is raised to about 95 C. with agitation andsulfamic acid is added in quantity to convert the adduct into a sulfatedproduct. The temperature is elevated during the reaction to about 115(3., and the resulting mass of reaction products is permitted to cool toap proximately C. A solution of an alkali hydroxide, containing about 40parts by weight of the hydroxide dissolved in about 150 parts by weightof water, is then added to the reaction mass, preferably in smallincrements. The rate of addition is controlled so that ammonia evolvedcan be released from the system without excessive foaming. Afteraddition of about one-half of the caustic solution, there is evidence ofgel formation with slow release of ammonia. At this point, approximately60 parts by weight of methanol are added to the reaction mass to lowerthe viscosity and to permit continuing addition of the caustic solution.When all caustic has been added, about 30 parts by weight of methanoland 58 parts by weight of water are added and the temperature of thereaction mass is raised to about to C. to complete removal of ammonia.

While the above description of the reaction illustrates sulfamic acid inuse as the sulfating agent, it will be obvious to those skilled in theart that any of the common sulfating agents, such as sulfuric acid,oleum, sulfur trioxide or chlorosulfonic acid, may be used instead ofsulfarnic acid; and minor changes in the above process can be madeaccording to well known principles of conducting a sulfation reaction.In any case, the neutralized product is an alkalized salt of a sulfatedadduct made by adducting the alkylphenol still bottoms with ethyleneoxide. Sodium hydroxide is a preferred alkali hydroxide and the sodiumsalt is the preferred product.

In general, the manipulative steps of the present flotation process arevery similar to those of the prior art except for the presence of theparticular novel collector mixture used. A finely ground barite ore ispulped with water and is agitated and aerated, usually in the presenceof about .8 to 4.0 pounds per ton of sodium silicate, sulficient sodiumhydroxide to give a desired pulp pH which preferably is in the rangefrom about 9.0' to 11.0 with an optimum of about 10.5, suihcientfrothing agent to form the desired froth, and the collector, which is amixture of fatty acid and the sodium salt of sulfated still bottomsadduct described above. While sodium hydroxide is the preferred materialfor control of pH, it is to be understood that other alkalis such aspotassium hydroxide may be used.

The following examples illustrate typical results in conducting thefiotation of baiite in the presence of the novel mixture of collectingagents.

EXAMPLE I Laboratory-scale tests were conducted on a barite ore fromsouthwest Arkansas, containing, in addition to barite, calcite, somepyrite and silica. These tests were conducted in a series of pH rangesfrom 8.1, the natural pH of an aqueous pulp of this ore, up to 12.0. Theincrease in pH was attained by the addition in increased quantities ofsodium hydroxide. In each of the tests recorded in the following table,0.75 pound of sodium salt of sulfated nonylphenol still bottoms adductedwith about twice its weight of ethylene oxide was used in I connectionwith 1.5 pounds per ton of a fatty acid fraction distilled from tall oilcontaining approximately 50 percent oleic, 40 percent linoleic, 4percent linolenic and 7 about 6 percent residual rosin acids as thecollecting agent. The following results were obtained:

TEST NO. 4G78pH, s.1rns. PEP. TON NaOH, 0.

TON NaOH, at

TEST NO. 4SS3pH, fill-LBS. PER TON NQOII, 1.0

TEST NO. 4684 DH, 11.5-LBS. PER TON NaOH, 1.7

Cone 71. 6 4.199 Q0. 0 94. 4 lvlids. 12. 7 3. 007 21. 4 3. 9 Tails 15. 72. 830 7. 5 1. 7

TEST NO. 4685-}1H, 12.0-LBS. PER TON NaOH, 3.0

75. 2 4. 134 88.1 95. 8 13.1 2. 927 15. 3 2. 9 ll. 7 2. S 7. 5 1. 3

It will be observed from the above results that barium sulfate recoverywas excellent in all ranges from pH 8.1 to 12.0, ranging from 88.3% atpH 8.1 to 95.8% at pH 12.0. However, the purity of the concentrateincreased with increasing pH from 8.1 up to a maximum at pH 9.5 andslowly decreased with increasing pH above that point. Thus, thepreferred pH range for carrying out our process will be found in therange from about 9.0 to about 11.0, with an optimum pH of about 10.5,based upon total recovery and purity of the concentrated material.

EXAMPLE I1 Full-plant-scale tests were conducted using the novelcombination of collecting agents of the present invention, using thesame type of southwest Arkansas barite ore used in the laboratory-scaleexperiments. This plant was operated on a 16-hour-per-day schedule for aperiod of two weeks. Each day was divided into two 8-hour shifts; and inthe first week, the collecting agents of this invention were used duringthe first 8-hour shifts and a combination of cetyl-stearyl sulfate andfatty acids from tall oil was used during the second 8-hour shifts.During the second week, the shifts using the diti rent combinations werereversed in order to balance out any stop and start variables which werepresent.

In n hi t each Week, the reagents used were 0.8

pound per ton of sodium hydroxide, giving the pulp a pH of 10.6, 0.79pound per ton of sodium salt of sulfated adduct of nonylphenol stillbottoms, and 0.44 pound per ton of a fatty acid fraction derived fromthe distillation of tall oil. During the other shift, the reagents usedwere 1.0 pound per ton of sodium hydroxide, giving the pulp a pH of11.0, 1.41 pounds per ton of cetyl-stear l sulfate, and 0.46 pound perton of fatty acids derived from tall oil.

In each shift, identical quantities of sodium silicate and frothingagent were used. The cetyl-stearyl sulfatedatty acid combination wasused as a comparison collector material because it was believed thatthis mixture was the most efficient collector known at the time thetests were run. The following results were obtained:

RESULTS USING SODIUBI SALT SULFATED ADDUCT OF NONYLPEENOL STILL BOTTONISAND FATTY ACID Percent wt. BaSO Percent recovered content. of BaSOi Sp.gr.

fraction recovered Feed 190. 0 68.1 3. 68 G5. 4 92. 7 89. 0 4. 25 34. 621. 6 3 01 that the salt of the sulfated adduct of nonylphenol stillbottoms is commercially available as a liquid resulted in decreased timerequired for solution of the reagents in water, and the solubility ofthe new combination of re- 7 agents is such that no heating of Water isrequired for its solution.

From the foregoing, it will be seen that this invention is one welladapted to attain all of the ends and objects hereinabove set forth,together with other advantages which are obvious and which are inherentto the process and method.

It will be understood thatcertain features and subcomhinations are ofutility and may be employed witnout reference to other features andsubcombinations. This is contemplated by and is within the scope of theclaims.

The invention having been described, what is claimed 1. In afroth-flotation process for; separating barite from gangue wherein afinely ground barite ore is suspended in water, the resulting pulpisagitated and aerated in the presence of a collecting agent, and bariteis recovered from the froth, that improvement which comprises carryingout froth-flotation in the presence of a fatty acid having 8 to 20carbon atoms per molecule and an alkali metal salt of a sulfated stillbottoms adduct, made by adducting a still bottoms, derived from aprocess for alkylating phenol with a polymerized alkene, with from 1.5to 3.0 times its weight of ethylene oxide, sulfating the adduct andneutralizing the resulting product with an alkali hydroxide, wherein thealkene polymerized contains from 2 to 4 carbon atoms.

2. In a froth-flotation process for Separating barite.

in the presence of a collecting agent, and barite is recov- 100. 0 68. 43. (i9 (i5. 8 92. 7 89. 2 4. 25 34. 2 21. 6 3. 01 V ered from the froth,that improvement which comprises carrying out froth-flotation in thepresence of a fatty acid having from 8 to 20 carbon atoms per moleculeand an alkali metal salt of a sulfated adduct made by adductingnonylphenol still bottoms with about 1.5 to 3.0 times its Weight ofethylene oxide, sulfating the adduct and neutralizing the product Wtihan alkali hydroxide.

3. The process of claim 2 wherein the fatty acid component is a mixtureof fatty acids distilled from tall oil.

4. The process of claim 2 wherein the salt of the sulfated nonylphenolstill bottoms adduct and fatty acids are present in proportions of about10:1 to about 1:2.

5. The process of claim 2 wherein the salt of the sulfated nonylphenolstill bottoms adduct and fatty acids are present in proportions of about2:1 to about 1:2.

6. The process of claim 1 conducted in the presence of an alkali metalhydroxide in quantity sufficient to give a pulp pH in the range from 9.0to 11.0.

7. The process of claim 5 conducted in the presence of sufiicient sodiumhydroxide to give a pulp pH of about 10.5.

8. The process of claim 2 wherein the alkali metal salt of sulfatednonylphenol still bottoms is a sodium salt.

References Cited in the file of this patent UNITED STATES PATENTS2,230,565 Gaylor Feb. 4, 1941 2,302,338 Moeller Nov. 17, 1942 2,547,148Bates Apr. 3, 1951 2,647,629 Velt-nan Aug. 4, 1953 2,834,463 Vincent May13, 1958 2,970,692 Henderson Feb. 7, 1961 FOREIGN PATENTS 861,579 FranceOct. 28, 1940

1. IN A FROTH-FLOTATION PROCESS FOR SEPARATING BARITE FROM GANGUEWHEREIN A FINELY GROUND BARITE ORE IS SUSPENDED IN WATER, THE RESULTINGPULP IS AGITATED AND AERATED IN THE PRESENCE OF A COLLECTING AGENT, ANDBARITE IS RECOVERED FROM THE FROTH, THAT IMPROVEMENT WHICH COMPRISESCARRYING OUT FROTH-FLOTATION IN THE PRESENCE OF A FATTY ACID HAVING 8 TO20 CARBON ATOMS PER MOLECULE AND AN ALKALI METAL SALT OF A SULFATEDSTILL BOTTOMS ADDUCT, MADE BY ADDUCTING A STILL BOTTOMS, DERIVED FROM APROCESS FOR ALKYLATING PHENOL WITH A POLYMERIZED ALKENE, WITH FROM 1.5TO 3.0 TIMES ITS WEIGHT OF ETHYLENE OXIDE, SULFATING THE ADDUCT ANDNEUTRALIZING THE RESULTING PRODUCT WITH AN ALKALI HYDROXIDE, WHEREIN THEALKENE POLYMERIZED CONTAINS FROM 2 TO 4 CARBON ATOMS.